Azobisisobutyronitrile → Methyl 3-bromo-4-(bromomethyl)benzoate

HRID 230014Notes

Reaction equation

HRID 230014 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6].[Br:13]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH2:12][Br:13])[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 7015747Methyl 3-bromo-4-methylbenzoate

Product 1

HCID 10804694Methyl 3-bromo-4-(bromomethyl)benzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

To a solution of 1.09 g (4.76 mmol) of the product from Example 224 Step A in 7 mL of carbon tetrachloride was added 847 mg (4.76 mmol) of N-bromosuccinimide and 78 mg (0.48 mmol) of 2,2′-azobisisobutyronitrile. The resultant mixture was heated at reflux for 2 5 hours, cooled to ambient temperature, diluted with carbon tetrachloride and filtered through celite. The filtrate was concentrated in vacuo and carried on without purification assuming 100% conversion. HPLC/MS (ESI) m/z (M+H)=310.9 (3.68 min).

Workup

  1. temperatureat reflux for 2 5 hours
  2. filtrationfiltered through celite
  3. concentrationThe filtrate was concentrated in vacuo
  4. customcarried on without purification
  5. customHPLC/MS (ESI) m/z (M+H)=310.9 (3.68 min)

Sources & evidence

ORD record
ord-9718766ead334480b6cec93aef000a77
Source dataset
uspto-grants-2009_07
Patent number
US07563815B2

Reaction notes

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